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Puerto Rico Cruises Starting In October 2026, 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in October 2026, 2027 or 2028, we have 30 unique cruise itineraries and 145 departures available, operated by eight of the world's leading cruise lines departing in October.
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30 Cruises (145 Departures)
30 Cruises (145 Departures)
Departures
Duration
8 Days
20 Days
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$700pp
$28,480pp
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13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (2)

13 Days (12 Nights) Barcelona to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visits: Spain, Morocco, Puerto Rico
Inside
$1,864
Oceanview
$2,112
Balcony
$2,116
Suite
$6,835
From (Per Person)
A$1,864
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,452
Oceanview
$1,779
Balcony
$2,066
Suite
-
From (Per Person)
A$1,452
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,238
Oceanview
$1,347
Balcony
$1,673
Suite
-
From (Per Person)
A$1,238
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$895
Oceanview
$995
Balcony
$1,133
Suite
$1,855
From (Per Person)
A$895
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,185
Oceanview
$1,432
Balcony
$1,789
Suite
$6,669
From (Per Person)
A$1,185
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking
Ship: Viking Sea
Departure: 23 October 2026
Visits: Spain, Portugal, Sint Maarten, Puerto Rico
Exclusive Savings
Balcony
$5,826
Suite
$9,354
From (Per Person)
A$5,826
Save 1,369
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,711
Oceanview
$2,221
Balcony
$2,024
Suite
-
From (Per Person)
A$1,711
Save 919
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Jun 2027 to Oct 2027
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,555
Oceanview
$1,663
Balcony
$1,746
Suite
$3,936
From (Per Person)
A$1,555
Save 1,166
Per Person
View Trip
10 Day New York to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) New York to San Juan
Cruise Line: Crystal
Ship: Crystal Symphony
Departure: 26 October 2026
Visits: USA, Bermuda, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$5,540
Balcony
$6,840
Suite
$7,445
From (Per Person)
A$5,540
Save 1,160
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Aug 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,750
Suite
$2,182
From (Per Person)
A$865
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: Jul 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,908
Oceanview
$2,136
Balcony
$2,192
Suite
$3,695
From (Per Person)
A$1,908
Save 2,172
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jul 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,870
Oceanview
$2,289
Balcony
$2,218
Suite
$4,170
From (Per Person)
A$1,870
Save 1,525
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,365
Oceanview
$1,552
Balcony
$1,492
Suite
$5,344
From (Per Person)
A$1,365
Save 861
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,170
Oceanview
$1,527
Balcony
$1,944
Suite
$3,807
From (Per Person)
A$1,170
Save 701
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Jul 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$982
Oceanview
$1,220
Balcony
$1,517
Suite
$2,309
From (Per Person)
A$982
Save 22
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (4)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,579
Oceanview
$2,981
Balcony
$3,785
Suite
$6,460
From (Per Person)
A$2,579
Save 52
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,064
Oceanview
-
Balcony
$1,070
Suite
$1,687
From (Per Person)
A$1,064
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,030
Oceanview
$1,137
Balcony
$1,594
Suite
$2,574
From (Per Person)
A$1,030
Save 701
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,978
Oceanview
$1,988
Balcony
$2,661
Suite
$10,658
From (Per Person)
A$1,978
Per Person
View Trip
20 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

20 Days (19 Nights) Genoa to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$2,236
Oceanview
$2,365
Balcony
$3,176
Suite
-
From (Per Person)
A$2,236
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visits: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,547
Oceanview
$2,854
Balcony
$3,398
Suite
$5,764
From (Per Person)
A$2,547
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,749
Oceanview
$2,060
Balcony
$2,268
Suite
$6,099
From (Per Person)
A$1,749
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,750
Oceanview
$1,859
Balcony
$2,146
Suite
-
From (Per Person)
A$1,750
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,889
Oceanview
$1,948
Balcony
$2,265
Suite
$10,156
From (Per Person)
A$1,889
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,101
Oceanview
$1,203
Balcony
$1,834
Suite
$2,294
From (Per Person)
A$1,101
Save 1,074
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 04 October 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,493
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,493
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,401
Oceanview
$1,805
Balcony
$1,774
Suite
$4,151
From (Per Person)
A$1,401
Save 963
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,080
Oceanview
$1,245
Balcony
$2,391
Suite
$3,493
From (Per Person)
A$1,080
Save 645
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,192
Oceanview
$1,390
Balcony
$1,529
Suite
$2,083
From (Per Person)
A$1,192
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,591
Oceanview
$1,663
Balcony
$1,937
Suite
$6,110
From (Per Person)
A$1,591
Save 892
Per Person
View Trip
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